EP2326613B1 - Producing 2,3,3,3-tetrafluoropropene - Google Patents

Producing 2,3,3,3-tetrafluoropropene Download PDF

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Publication number
EP2326613B1
EP2326613B1 EP09788047.0A EP09788047A EP2326613B1 EP 2326613 B1 EP2326613 B1 EP 2326613B1 EP 09788047 A EP09788047 A EP 09788047A EP 2326613 B1 EP2326613 B1 EP 2326613B1
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Prior art keywords
hfo
water
mixture
stream
water content
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EP09788047.0A
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German (de)
English (en)
French (fr)
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EP2326613A2 (en
Inventor
Kazuhiro Takahashi
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Daikin Industries Ltd
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Daikin Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/10—Liquid materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/24—Only one single fluoro component present
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/32—The mixture being azeotropic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2205/00—Aspects relating to compounds used in compression type refrigeration systems
    • C09K2205/40—Replacement mixtures

Definitions

  • the present invention relates to a process for producing 2,3,3,3-tetrafluoropropene with a reduced water content by utilizing the properties of the azeotropic or azeotrope-like composition.
  • HFO-1234yf is obtained as a mixture of HFO-1234yf with HF, and it is thus necessary to remove HF by using some method.
  • HFO-1234yf treated by this method is always intermixed with steam mist, or water in an amount corresponding to the vapor pressure.
  • sources of water such as water contained in the starting materials, water derived from the catalyst, and water remaining in the equipment.
  • the obtained HFO-1234yf is intermixed with these waters.
  • the water contained in the final product HFO-1234yf affects the performance of HFO-1234yf as a refrigerant, as well as its stability and corrosivity to the device. Therefore, the removal of water is an important factor in quality control, and a method for removing water is a particularly important technique.
  • a common method for removing water is the use of an adsorbent, such as a molecular sieve.
  • an adsorbent such as a molecular sieve.
  • WO 2007/144632 discloses a method comprising drying liquid HFO-1234yf over zeolite.
  • this method requires the high-speed treatment of a gas having a comparatively low water content, thus necessitating the use of a large dehydrating tower.
  • periodic reactivation or replacement of the adsorbent is also necessary, and industrial waste is generated in large amounts during the replacement of the adsorbent.
  • a primary object of the invention is to provide a method for efficiently removing water from HFO-1234yf.
  • the present inventors carried out extensive research to achieve the above object. As a result, the inventors discovered an unknown phenomenon that HFO-1234yf and water form a minimum boiling point azeotropic composition (an azeotropic composition wherein liquid-liquid separation occurs is referred to as a heterogeneous azeotropic composition). Further, the inventors found that water can be efficiently removed from HFO-1234yf by utilizing the azeotropic property. The present invention has been accomplished based on this finding.
  • the present invention provides a process for producing HFO-1234yf, comprising distilling a mixture of water and HFO-1234yf to separate the mixture into a first stream and a second stream, the first stream containing HFO-1234yf with a water content higher than that of the original mixture, and the second stream containing HFO-1234yf with a water content lower than that of the original mixture; and obtaining HFO-1234yf with a reduced water content from the second stream.
  • azeotropic or azeotrope-like composition as well as the process for producing HFO-1234yf of the present invention are described below in more detail.
  • the azeotropic or azeotrope-like composition comprises HFO-1234yf and water.
  • HFO-1234yf and water form a minimum boiling point azeotropic composition.
  • the specific azeotropic composition varies depending on the temperature and pressure. For example, when the pressure is 0.55 MPa and the temperature is 16°C, the composition consisting of 99.979 wt.% of HFO-1234yf and 0.021 wt.% of water is an azeotropic composition.
  • the pressure to be applied in distillation to remove water is preferably in the range of atmospheric pressure to 2 MPa, as described below.
  • the pressure is within this range, a mixture of 99-99.995 wt.% of HFO-1234yf and 0.005-1 wt.% of water forms an azeotropic or azeotrope-like composition.
  • azeotropic composition refers to a mixture wherein the vapor phase in equilibrium with the liquid phase has a composition identical to that of the liquid phase.
  • azeotrope-like composition refers to a mixture wherein the vapor phase in equilibrium with the liquid phase has a composition similar to that of the liquid phase.
  • a mixture of HFO-1234yf and water is first distilled.
  • the distillation may be performed at a pressure in the range of atmospheric pressure (0.1013 MPa) to 2 MPa.
  • An overly low pressure results in a low reflux temperature, and liquid-liquid phase separation may occur in the distillation column. Therefore, the distillation is preferably performed at a pressure in the range of 0.4-2 MPa.
  • the water content of the starting HFO-1234yf is not particularly limited, there is a limit to the mutual solubility of HFO-1234yf and water. If the water content of the starting HFO-1234yf is too high, liquid-liquid separation may occur in the rectification column, which results in a three-phase distillation, thus reducing the efficiency of the column. Accordingly, before feeding into the rectification column, a decanter, etc. may be used to separate the starting HFO-1234yf into an aqueous phase and an HFO-1234yf-rich organic phase to reduce the water content of HFO-1234yf somewhat, and then HFO-1234yf with a reduced water content may be fed into the rectification column.
  • a mixture of 99-99.995 wt.% of HFO-1234yf and 0.005-1 wt.% of water i.e., a mixture having a water content of 50-10,000 ppm (expressed by weight; the same hereinafter) forms an azeotropic or azeotrope-like composition.
  • a mixture of water and HFO-1234yf having a water content lower than that of the azeotropic composition is distilled, a mixture of water and HFO-1234yf with a concentrated water, i.e., a mixture of water and HFO-1234yf whose water content is higher than that of the original mixture fed to the distillation column can be obtained from the top of the column.
  • the drying tower to be used can be downsized compared to conventional methods.
  • the mixture of HFO-1234yf and water obtained from the top of the column is cooled using a decanter or the like to separate the mixture into a liquid phase A with a high water content and a liquid phase B with a high HFO-1234yf content, water can be more efficiently removed.
  • the mixture may be separated into two liquid phases by cooling to a temperature lower than the temperature of the mixture of HFO-1234yf and water withdrawn from the distillation column.
  • the cooling temperature may be a temperature at which the water obtained by the liquid-liquid separation does not freeze.
  • Water can be efficiently removed by performing the distillation and liquid-liquid separation as a continuous operation.
  • the phase with a high water content obtained by separation according to the above method may be discarded.
  • the phase with a high HFO-1234yf content may be returned to the distillation column and distilled again, or may be singly dried over a molecular sieve to remove water, thus enabling the drastic downsizing of the drying tower.
  • the HFO-1234yf with a reduced water content obtained from the bottom of the column can also dried over a molecular sieve or the like to remove water, thus enabling the removal of water using a small drying tower.
  • HFO-1234yf with a reduced water content can be obtained from a mixture of HFO-1234yf and water.
  • the distillate may contain impurities contained in HFO-1234yf, such as remaining unreacted 1,1,1,2,3-pentafluoropropane (HFC-245eb) and 1,1,1,2,2-pentafluoropropane (HFC-245cb) charged as starting materials for the dehydrofluorination reaction.
  • impurities may be withdrawn together with HFO-1234yf from the distillation column and removed by separation using another distillation column.
  • concentrating a specific component in a mixture means removing the components other than the specific component from the mixture.
  • water-containing HFO-1234yf obtained by various synthesizing methods is subjected to distillation utilizing the azeotropic properties of HFO-1234yf and water, and optionally further subjected to liquid-liquid separation to efficiently remove water, whereby HFO-1234yf with a reduced water content can be easily produced.
  • HFO-1234yf containing 50 ppm of water was fed to an intermediate tray of a rectification column 2 m in height and 7 cm in diameter at a rate of 10 kg/hr (stream F11), and rectified under the following conditions: column operating pressure: 0.6 MPa; column top temperature: 21°C; reflux ratio: 16.
  • HFO-1234yf with an increased water content was withdrawn from the top of the column and fed to a decanter at a rate of 1 kg/hr (Stream S11). By cooling to 2°C, liquid-liquid phase separation was allowed to proceed. The lower layer was returned to the top of the column (Stream S14), and the upper layer was isolated as a water-rich layer (Stream S13).
  • HFO-1234yf with a reduced water content (Stream S12) was obtained from the bottom of the column at a rate of 9 kg/hr.
  • Table 1 shows the results of measuring the water content of each stream by a Karl Fischer moisture meter.
  • Table 1 Water content (by weight) F11 S11 S12 S13 S14 50 ppm 200 ppm 3 ppm 90% 30 ppm
  • HFO-1234yf containing 50 ppm of water was fed to an intermediate tray of a rectification column 2 m in height and 7 cm in diameter at a rate of 10 kg/hr (Stream F11), and rectified under the following conditions: column operating pressure: 0.6 MPa; column top temperature: 21°C; and reflux ratio: 16.
  • HFO-1234yf with an increased water content was withdrawn from the top of the column at a rate of 1 kg/hr (Stream S11), fed to a drying tower containing a molecular sieve, and dried (Stream S13).
  • HFO-1234yf with a reduced water content was obtained from the bottom of the column at a rate of 9 kg/hr (Stream S12).
  • Table 2 shows the results of measuring the water content of each stream by a Karl Fischer moisture meter.
  • Table 2 Water content (by weight) F11 S11 S12 S13 50 ppm 200 ppm 3 ppm 5 ppm
  • HFO-1234yf containing 50 ppm of water was fed to an intermediate tray of a rectification column 2 m in height and 7 cm in diameter at a rate of 10 kg/hr (Stream F11), and rectified under the following conditions: column operating pressure: 0.6 MPa; column top temperature: 21°C; and reflux ratio: 16.
  • HFO-1234yf with an increased water content was withdrawn from the top of the column and fed to a decanter at a rate of 1 kg/hr (Stream S11). By cooling to 2°C, liquid-liquid separation was allowed to proceed. The lower layer was withdrawn as a liquid (Stream S14) and dried by being passed through a drying tower containing molecular sieve 4A (Stream S15). The upper layer was isolated as a water-rich layer (Stream S13). HFO-1234yf with a reduced water content was obtained from the bottom of the column at a rate of 9 kg/hr (Stream S12).
  • Table 3 shows the results of measuring the water content of each stream by a Karl Fischer moisture meter.
  • Table 3 Water content (by weight) F11 S11 S12 S13 S14 S15 50 ppm 200 ppm 3 ppm 90% 30 ppm 5 ppm

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Combustion & Propulsion (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP09788047.0A 2008-08-26 2009-08-21 Producing 2,3,3,3-tetrafluoropropene Active EP2326613B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9178308P 2008-08-26 2008-08-26
PCT/JP2009/065023 WO2010024366A2 (en) 2008-08-26 2009-08-21 Azeotropic or azeotrope-like composition and process for producing 2,3,3,3-tetrafluoropropene

Publications (2)

Publication Number Publication Date
EP2326613A2 EP2326613A2 (en) 2011-06-01
EP2326613B1 true EP2326613B1 (en) 2018-10-10

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EP09788047.0A Active EP2326613B1 (en) 2008-08-26 2009-08-21 Producing 2,3,3,3-tetrafluoropropene

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US (2) US8853473B2 (zh)
EP (1) EP2326613B1 (zh)
JP (2) JP5370479B2 (zh)
CN (1) CN102131754B (zh)
WO (1) WO2010024366A2 (zh)

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US8951431B2 (en) * 2010-05-06 2015-02-10 E I Du Pont De Nemours And Company Azeotrope-like compositions of pentafluoropropene and water
US8747691B2 (en) * 2010-05-06 2014-06-10 Honeywell International Inc. Azeotrope-like compositions of tetrafluoropropene and water
JP6056771B2 (ja) * 2011-12-28 2017-01-11 旭硝子株式会社 ２，３，３，３−テトラフルオロプロペンの精製方法、精製装置および製造方法
MX362043B (es) * 2013-03-15 2019-01-07 Chemours Co Fc Llc Proceso para la reduccion de impurezas de alquino en fluoroolefinas.
EP3549995A1 (en) 2014-09-26 2019-10-09 Daikin Industries, Ltd. Haloolefin-based composition
PL3018183T3 (pl) 2014-09-26 2023-03-13 Daikin Industries, Ltd. Kompozycja na bazie fluorowcoolefiny i jej zastosowanie
US10029964B2 (en) * 2016-08-30 2018-07-24 Honeywell International Inc. Azeotropic or azeotrope-like compositions of 3,3,3-trifluoropropyne and water
CN110035988A (zh) * 2016-12-02 2019-07-19 霍尼韦尔国际公司 用于干燥hcfo-1233zd的方法
GB2562103A (en) * 2017-05-05 2018-11-07 Mexichem Fluor Sa De Cv Process
JP6485493B2 (ja) * 2017-06-16 2019-03-20 ダイキン工業株式会社 ペンタフルオロプロパンと水とを含む共沸又は共沸様組成物、並びにペンタフルオロプロパンの製造方法
US20220080243A1 (en) * 2020-09-11 2022-03-17 Honeywell International Inc. Azeotrope or azeotrope-like compositions of trifluoroiodomethane (cf3i) and water

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US20050054743A1 (en) 1999-03-15 2005-03-10 Bement Leslie Bruce Azeotrope-like compositions of pentafluoropropane and water
US20080051612A1 (en) 2006-08-24 2008-02-28 E. I. Dupont De Nemours And Company Processes for separation of fluoroolefins from hydrogen fluoride by azeotropic distillation
WO2008075017A2 (en) 2006-12-19 2008-06-26 Ineos Fluor Holdings Limited Process for the preparation of c3-7 fluoroalkenes by base-mediated dehydrohalogenatation of hydrohalogenated c3 -7 fluoroalkanes
WO2009052064A2 (en) 2007-10-15 2009-04-23 Honeywell International Inc. Processes for synthesis of fluorinated olefins

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US5514251A (en) 1993-04-01 1996-05-07 Solvay (Societe Anonyme) Process for the removal of water from a solution by azeotropic distillation and process for the production of a hydrofluoroalkane
US20050054743A1 (en) 1999-03-15 2005-03-10 Bement Leslie Bruce Azeotrope-like compositions of pentafluoropropane and water
US20080051612A1 (en) 2006-08-24 2008-02-28 E. I. Dupont De Nemours And Company Processes for separation of fluoroolefins from hydrogen fluoride by azeotropic distillation
WO2008075017A2 (en) 2006-12-19 2008-06-26 Ineos Fluor Holdings Limited Process for the preparation of c3-7 fluoroalkenes by base-mediated dehydrohalogenatation of hydrohalogenated c3 -7 fluoroalkanes
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US8853473B2 (en) 2014-10-07
US20140367606A1 (en) 2014-12-18
WO2010024366A2 (en) 2010-03-04
CN102131754B (zh) 2015-02-25
JP2014001393A (ja) 2014-01-09
US10011753B2 (en) 2018-07-03
CN102131754A (zh) 2011-07-20
WO2010024366A3 (en) 2010-05-06
JP2012500185A (ja) 2012-01-05
US20110160500A1 (en) 2011-06-30
EP2326613A2 (en) 2011-06-01
JP5370479B2 (ja) 2013-12-18
JP5742893B2 (ja) 2015-07-01

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